Page 1 of 34 UNITED STA

TES ENVIRONMENTA L PROTECTION A GENCY WASHINGTON, D.C. 20460 OFFICE OF PREVENTION, PESTICIDE AND TOXIC SUBSTANCES

MEMORANDUM Date : 03 / 03 / 2010 . SUBJECT: Halosulfuron - methyl. Application for Section 3 Registration o f Sandea®

Herbicide (EPA Reg. No. 81880 - 18) and GWN - 3061 Herbicide (EPA Reg. No. 81880 - 2) t o Add New Uses on : Pea and Bean, Succulent Shelled, Subgroup 6B; Vegetable, Tuberous and Corm, Subgroup 1C; Rhubarb; Bushberry Subgroup 13 - 07B; Pea and Bean, Dried Shelled, Except Soy bean, Subgroup 6C; Apple; and Okra. Summary

of Analy tical Chemistry

and Residue Data . PC Code: 128721 DP Barcode: D 367058 Decision No.: 414896 Registration No s . : 81880 - 18 and 81880 - 2 Petition No.: 9E7577 Regulatory Action: Sect ion 3 Registration Risk Assessment Type: NA Case No.: NA T XR No.: NA CAS No.: 100784 - 20 - 1 MRID No s .: 47772101 through 47772106 40 CFR: § 180.479 FROM: Debra Rate, Ph.D., Biologist

Alternative Risk Integration and Assessme nt (ARIA) Team Risk Integration, Minor Use and Emergency Response Branch (RIMUERB) Registration Division (RD; 7505P) THROUGH: Steve Funk , Senior Scientist

Risk Assessment Branch I II ( RA BIII) Health Effects Division ( HED ; 7509P) TO: Whang Phang, Ph .D., Toxicologist

RABI II/HED (7509P) Barbara Madden Minor Use Team RIMUERB/RD (7505P) This document was originally prepared under contract by Dy namac Corporation . The document has been reviewed by ARIA/HED and revised to reflect current Office of Pes ticide Programs (OPP) policies.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 2 of 34 Executive Summary Halosulfuron - methyl is a selective herbicide belonging to the su lfonylurea group of herbicide s . It s mode of action includes the inhi bit ion of a specific plant enzy me , acetolacetate sy

nthase . Halosulfuron - methyl is registered for the pre - and postemergence control of annual broadleaf weeds and nutsedges in selected crops, as well as residential turf grass and ornamentals . Halosulfuron - methyl is sold in the U.S. as a dry flowable/water - dispersible granule formulation. The petitioner, Interregional Research Project No. 4 (IR - 4), has proposed new uses of halosulfuron - methyl on : apple ; bushberry Subgroup 13 - 07B ; okra ; succulent - shelled p ea and bean Subgroup 6B; dried shelled pea and bean, except soy bean, Subgroup 6 C ; rhubarb ; and tuberous and corm vegetable Subgroup 1C. Inconjunction with the requested amended use, IR - 4 has submitted a petition, PP# 9E7577 , to propose the establishment o f permanent tolerance s for residues of the herbicide halosulfuron - methyl ( methyl 3 - chloro - 5 - [[[[ (4,6 - dimethoxy- 2 - py rimidinyl )amino]carbonyl]amino]sulfonyl] - 1 - methyl - 1H - py razole - 4 - carboxylate) in/on the following raw agricultural commodit ies : Pea and bean, succulent shelled, Subgroup 6B ................................ ... 0.05 ppm Vegetable, tuberous and c orm, Subgroup 1C ................................ ...... 0.05 ppm Rhubarb ................................ ................................ ............................... 0.05 ppm Pea and bean, dried shelled, except soy bean, Subgroup 6C ................ 0.05 ppm Apple ................................ ................................ ................................ ... 0.05 ppm Okra ................................ ................................ ................................ ..... 0.05 ppm Bushberry , Subgroup 13 - 07B ................................ .............................. 0.05 ppm The end - use products relevant to this registration action are Sandea® Herbicide (EPA Reg. No. 81880 - 18) and GWN - 3061 Herbicide (EPA Reg. No. 81880 - 2). Both products are currently registered to Gowan Company and are classified as water - dispersible granular (WG) fo rmulation s containing 75% halosulfuron - methyl. The formulations are proposed for broadcast soil or foliar applications at maximum seasonal rates of 0.0 23 - 0.094 lb ai/A depending on the crop. Only

ground equipment in ≥15 gal/A of water may be used for applications; certain crops require the addition of no n - ionic surfactants in the spray mixture for enhanced control. The proposed preharvest intervals (PHI s ) range from 14 to 60 day s. Permanent tolerances are established under §180.479(a)(1) for residues of halosulfuron - methyl and its metabolites and degradates determined as 3 - chloro - 1 - methyl - 5 - sulfamoylpy razole - 4 - carboxylic acid, expressed as halosulfuron - methyl equivalent in/on the meat by products of cattle, goat, hog, horse, and sheep at 0.1 ppm. Tolerances are established under §180.479(a)(2) for residues of halosulfuron - methyl in/on a variety of field, fruit, and vegetable crop commodities, at levels r anging from 0.05 to 2.0 ppm. A time - limited tolerance for sweet potato established under §180.479(b) has expired (expiration data 12/31/ 20 08). The nature of the residue in plants is adequately understood based on acceptable metabolism studies with corn, sugarcane, and soy bean treated both pre - and postemergence . The terminal residue of concern in plants is halosulfuron - methyl.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 3 of 34 The nature of the residue in ruminants is adequately understood based on an acceptable goat metabolism study . T he residue of co ncern in ruminants is halosulfuron - methyl; however, because the approved enforcement method for livestock commodities quantifies the parent compound and metabolites containing the 3 - chlorosulfonamide moiety (3 - CSA) by

converting residues to 3 - CSA, toleranc es for residues in livestock commodities are expressed in terms of halosulfuron - methyl and its metabolites determined as 3 - CSA, expressed as halosulfuron - methyl equivalents. There are no poultry feedstuffs associated with the recommended tolerances and cr op uses addressed in this action. Therefore, a discussion of the metabolism of halosulfuron methyl in poultry and hogs is not germane to this petition. Adequate analy

tical methods are available for the enforcement of tolerances for residues of halosulfur on - methyl in plants (Method RES - 109 - 97 - 4), and for residues of halosulfuron - methyl and its 3 - CSA metabolites in livestock commodities (Method RES - 046 - 93). The plant method determines halosulfuron - methyl as its rearrangement ester (RRE), and the livestock method converts residues of halosulfuron - methyl and metabolites containing the 3 - CSA moiety to 3 - CSA for determination. Samples from the submitted field trial and processing studies were analy zed for residues of halosulfuron - methyl using a modified versio n of the plant enforcement method with a petitioner - validated limit of quantitation (L OQ) of 0.0 5 ppm. A Biological and Economic Analy sis Division (BEAD/EPA) method validation for Method RES - 109 - 97 - 4 (MRI D 44495801) in rice straw, sugar cane, milo grain, field corn grain, cotton gin by products, and almond nutmeats indicated an LOQ of 0.05 ppm (DP#250584, G. Jeffrey Herndon, 10/28/ 19 98). Residues of halosulfuron - methyl and 3 - CSA are not adequately recovered by

FDA Multiresidue Method protocols . A dequate s torage stability data are available to support the storage conditions and durations of samples collected from the magnitude of the residue and processing studies on apples, blueberry , dry bean seed, succulent pea seed, potato tuber, potato processed commod ities, and rhubarb. As residues of halosulfuron - methyl were found to be stable in tested crop matrices, storage stability corrections need not be applied to the recommended tolerances for halosulfuron - methyl residues for these commodities. An adequate da iry

cattle feeding study

is available. Based on the re - evaluation of the feeding study relative to the re - calculated dietary burdens of 0. 468 ppm for beef cattle and 0. 825 ppm for dairy cattle , ARIA conclude s that tolerances for residues of halosulfuron - m ethyl need not be established for milk or meat, and fat of cattle, goat, hog, horse, and sheep. The established tolerance of 0.1 ppm for the meat by products of cattle, goat, hog, horse, and sheep are adequate for this registration action. The petitioner should note that if additional uses are proposed in the future which would result in an increase in the dietary burdens, ARIA/HED will re - assess the adequacy of established animal tolerances. Residues of halosulfuron - methyl were below the lowest limit o f method validation (L LM V; <0.05 ppm) in/on all commodity samples treated with the test formulation according to the conditions and parameters used in magnitude of the residue studies. The Agency ’s tolerance spreadsheet was not used for tolerance assessme nt.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 4 of 34 The submitted field trial data on apples and blueberries ( the latter is a representative commodity of Crop Subgroup 13 - 07B ) d id not reflect the use of a nonionic surfactant as recommended on the proposed label. The data will support a tolerance of 0. 05 ppm for apple . The data will support a tolerance of 0.05 ppm for the b ushberry Subgroup 13 - 07B provided the label for Sandea® Herbicide is amended to remove the instructions pertaining to the use of a non - ionic surfactant . I f it is IR - 4’s intention to add a nonionic surfactant when Sandea® Herbicide is applied to bushberry Subghroup 13 - 07B , then additional field trial data are required which include the use of an adjuvant . Inthe case of apples, the herbicide is applied to the orchard floor, and addit ion of a surfactant will have no effect on residues on the apples. No residue data were submitted to support the proposed use on okra. The ChemSAC meeting of 10/18/ 20 06 has recommended the inclusion of okra in Crop Group 8 (Fruiting Vegetables). The Che mSAC has also determined that a separate tolerance for okra should be listed in the appropriate section of the CFR entry until the new crop group regulation is published. The available field trial data for Fruiting Vegetables will be translated to okra. ARIA recommends a tolerance of 0.05 ppm for residues of halosulfuron - methyl in/on okra. The representative crops of Subgroup 6B are two commodities of: (1) any succulent shelled cultivar of bean (

Phaseolus spp.) or (2) immature soy bean seed ( Glycine max ) or (3) any Vigna spp. and garden pea (

Pisum spp.). The submitted field trial data for succulent peas were conducted at exaggerated rates (1. 4 X or 2. 8X ) , and the collected samples did not reflect the proposed 30 - day

PHI(the earliest PHI

tested was 55 day s ). The available data for succulent beans, previously

submitted under PP#1E06322 (DP#278587, A. Acierto , 6/15/ 20 02 ) to support the established individual tolerance of 0.05 ppm , also do not reflect the proposed use on Subgroup 6B because these data represe nt foliar application whereas the new proposed use pattern is for preemergence soil application. ARIA will not require additional data on succulent peas since treatment at 1X will likely result in residues below 0.05 ppm , even when harvested at a PHIof 3 0 - day s . Also, ARIA will not require additional data on succulent beans since soil treatment will l ikely

result in residues below 0.05 ppm. ARIA recommends for the proposed tolerance of 0.05 ppm for the Subgroup 6B (Pea and Bean, Succulent Shelled) pendin g a label revision to prohibit applications to legumes grown for livestock feeds because no residue data are available for cowpea forage and hay . Concomitant with the establishment of a tolerance for Subgroup 6 B, the individual tolerance for ‘bean, snap, succulent’ should be revoked. The representative commodities of Subgroup 6C are any one dried cultivar of bean ( Phaseolus spp.) and any

one dried cultivar of pea ( Pisum spp.) The submitted residue data for dry bean s reflect a single foliar broadcast appl ication conducted at ~1. 6 X the proposed application rate per crop cycle (or ~0. 8 X the proposed total application rate per year), the use of a nonionic surfactant, and the treated samples were collected approximating the proposed 30 - day PHI . Additional dat a for dry

beans were submitted under PP#1E06322 ( DP#278587, A. Acierto , 6/15/ 20 02 ) to support the established individual tolerance of 0.05 ppm. These data represent a single application of Permit 75 WG Herbicide at 0.032 lb ai/A made 0 to 6 day s after planting and an 86 - to 113 - day

PHI . ARIA is unable to recommend for the proposed use and tolerance of 0.05 ppm for Crop Subgroup 6C ( dried s helled b ean ( e xcept s oy bean ) and p ea ) because residue data on dried pea including the forages and hay of field pea cul tivars are required. When adequate residue data for dried pea s become available, the petitioner may again request a tolerance for Subgroup 6C .Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 5 of 34 The submitted field trial data on rhubarb were generated using slightly exaggerated rates of ~2.0 - 2. 1X . ARIA w ill not require additional data on rhubarb since treatment at 1X will likely result in residues below 0.05 ppm. The available data will support the proposed tolerance of 0.05 ppm for rhubarb. The submitted field trial data on potato, the representative c ommodity of Crop Subgroup 1C, do not fully conform to the OPPTS 860.1500 guideline as only 14 trials were conducted whereas the guideline requires a minimum of 16 trials to support a subgroup tolerance. In addition, the potato data were generated using ex aggerated rates of ~2.0 - 2. 1 X . At this exaggerated rate all potato residues were <0.05 ppm. Therefore, ARIA will not require additional data on potatoes since additional trials at a 1 X rate will l ikely result in residues below 0.05 ppm. The available dat a will support the proposed tolerance of 0.05 ppm for Crop Subgroup 1C. To fulfill the requirements for an apple processing data, a trial site was treated at ~5. 1X the proposed maximum seasonal rate to generate samples for processing; however, as residues were nondetectable in any

apple fruit sample s , processing was not initiated. These data are adequate to conclude that an additional apple processing study and tolerances for apple processed commodities are not required for this action. The submitted pro cessing data for potato are acceptable. Residues of halosulfuron - methyl were nonquantifiable (<0.05 ppm) in/on potato tubers following treatments at 2 X the proposed seasonal rate. Residues were also nonquantifiable in processed potato granules/flakes, ch ips, and wet peel. The Agency

would have preferred that a trial with an exaggerated rate equal to or higher than the maximum theoretical concentration factor of 5X for potato have been conducted. However, because of phy totoxicity limitations as reported in the magnitude of the residue trials, a new potato processing study will not be required. Based on these data, tolerances for potato processed commodities are not needed. Adequate confined and limited field rotational crop data are available. HED prev iously concluded that the residue of concern in rotational crops is halosulfuron - methyl . Based on the absence of the parent compound in the confined studies and in the limited field rotational crop studies, with the exception of one forage sample, HED pre viously concluded that rotational crop tolerances and restrictions are not required for halosulfuron - methyl. There are no Codex, Canadian, or Mexican maximum residue limits ( MRL s ) established for residues of halosulfuron - methyl in crop or livestock commod ities .Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 6 of 34 Regulatory Recommendations and Residue Chemistry Deficiencies ARIA has examined the residue chemistry database for halosulfuron - methyl and evaluated the adequacy of study submissions associated with the current action. Pendi ng submission of a revised Section B (see requirements under Directions for Use), a revised Section F (see requirements under c rop field trials) and the submission of standards for the 3 - CSA (3 - chlorosulfonamide acid) m etabolite and the RRE of halosulfuron - methyl (see requirements under Submittal of Analy

tical Reference Standards ), there are no residue chemistry data gaps that would preclude ARIA from recommending for registration for the following requested crops and/or crop subgroups. ARIA recommends for the establishment of to lerances for residues of the herbicide halosulfuron - methyl in/on the following raw agricultural commodities and/or crop subgroups: Pea and bean, succulent shelled, Subgroup 6B ................................ ... 0.05 ppm Vegetable, tuberous and corm, Subgroup 1C ................................ ...... 0. 05 ppm Rhubarb ................................ ................................ ............................... 0.05 ppm Apple ................................ ................................ ................................ ... 0.05 ppm Okra ................................ ................................ ................................ ..... 0.05 ppm Bushberry Subgroup 13 - 07B ................................ ............................... 0.05 ppm A human health risk assessment is forthcoming. Full un conditional registration for the recommended crop/crop subgroup uses (listed above) will be issued followi ng adequate resolution of the data gaps listed below. 860.1200 Directions for Use ● For Crop Subgroup 6B (p ea and b ean , s ucculent s helled ), the label (s) should be amended to prohibit applications to legumes grown for livestock feeds because no residue data are available for cowpea forage and hay . ● For Crop Subgroup 13 - 07B (b ushberry ), the label(s) should be amended to remove the instructions pertaining to the use of a non - ionic surfactant . I f it is IR - 4’s intention to add a nonionic surfactant when San dea® Herbicide is applied to these crops, then additional field trial data are required.

 F or Crop Subgroup 6C (dried pea and bean (except soy bean)) , the labels should be amended to remove the use directions for Crop Subgroup 6C . 860.1500 Crop Field Tri alsHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 7 of 34 ● Prior to granting a registration on Crop Subgroup 6C ( dried s helled pea and b ean ( e xcept s oy bean )), data on dried pea including the forages and hay of field pea cultivars are required from a minimum of five field trials. The requested field trials shoul d reflect total a pplication rates of 0.047 lb ai/A per crop cycle or 0.094 lb ai/A per year, a minimum 30 - day PHI , and the incorporation of a non - ionic surfactant in the spray mixture. A revised Section F should be submitted removing the request for Crop Subgroup 6C (dried shelled pea and bean (except soy bean)). 860.1650 Submittal of Analy tical Reference Standards ● Analy

tical reference standards for the 3 - CSA (3 - chlorosulfonamide acid) m etabolite and the RRE of halosulfuron - methyl must be submitted to the EPA National Pesticide Standards Repository . Modification to the Tolerance Expression as per HED’s Interim Gui dance on Tolerance Expressions (S. Knizner, 5/27/2009)

 40 CFR§180.479(a)(1):  Tolerances are established for residues of halosulfuron - methyl , methyl 5 - [(4,6 - dimethoxy- 2 - py

rimidiny )amino]carbonylaminosulfonyl] - 3 - chloro - 1 - methyl - 1 H - py razole - 4 - carboxylate , in cluding its metabolites and degradates , in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only those halosulfuron - methyl residues containing the 3 - chlorosulfonamide ( 3 - CSA ) m oiety , expressed as the stoichiometric equivalent of halosulfuron - methyl, in or on the commodity .  40 CFR§180.479(a)(2):  Tolerances are established for residues of halosulfuron - methyl , methyl 5 - [(4,6 - dimethoxy- 2 - py

rimidiny )amino]carbonylaminosulfonyl] - 3 - ch loro - 1 - methyl - 1 H - py razole - 4 - carboxylate , including its metabolites and degradates , in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only halosulfuron - methyl .Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 8 of 34 Background T he chemical structure s and nomenclature s of halosulfuron - methyl and the 3 - CSA moiety are presented in Table 1. The phy sicochemical properties of the technical grade of halosulfuron methyl are presented in Table 2. Table 1. Halosulfuron - me thyl Nom enclatu re . Chemical structure

N N C H 3 Cl

N N N H N H O S O O

O C H 3 O C H 3 O O C H 3

Common name halosulfuron - methyl Company experimental name MON 12000, NC - 319 IUPAC name methyl 3 - chloro - 5 - (4,6 - dimethoxypyrimidin - 2 - ylcarb amoyl sulf amoyl) - 1 - methylpyrazole - 4 - carboxylate CAS name methyl 3 - chloro - 5 - [[[[(4,6 - dimeth oxy - 2 - pyrimidinyl)amino]carbonyl]amino]sulfonyl] - 1 - methyl - 1 H - pyrazole - 4 - carboxylate CAS registry number 100784 - 20 - 1 End - use product (EP) 75% WG (SANDEA Herbicide; EPA Reg. No. 81880 - 18) 75% WG (GWN - 3061 Herbicide; EPA Reg. No. 81880 - 2) Chemical structur e of 3 - chlorosulfonamide moiety (3 - CSA) N N C H 3 Cl N H 2

S O O O H O

3 - chloro - 1 - methyl - 5 - sulfamoyl - 1 H - pyrazole - 4 - carboxylic acidHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 9 of 34 Table 2. Physicochem ical Properties of Halosulfuron - me thyl . Parameter Value Reference Melting range 175.5 - 177.2oC MRID 42139403; DP#s 173627 & 180565, 7/30/92, G.J. Herndon pH 4.11 at 25oC (1% w /v slurry) Density 1.618 g/mL at 25oC Water solubility at 20oC pH 5 0.0015 g/100 mL pH 7 0.165 g/100 mL pH 9 0.747 g/100 mL Solvent solubility at 20oC methanol 0.1616 g/100 mL n - hexane 0.001278 g/100 mL Vapor pressure <1 x 10 - 7 mm Hg at 25oC Dissociation constant, K a 3.61 x 10 - 4 at 22.4oC Octanol/water partition coefficient, Log(K OW ) at 23oC 1.67 at pH 5

- 0.0186 at pH 7

- 0.542 at pH 9 UV/visible absorption spectrum Not available 860.1200 Directio ns for Use The end - use products (EPs) relevant to this registration action are Sandea® Herbicide ( EPA Reg. No. 81880 - 18 ) and GWN - 3061 Herbicide ( EPA Reg. No. 81880 - 2 ) . Both products are currently registered to Gowan Company and are classified as WG formu lation s containing 75% halosulfuron - methyl . IR - 4 requests that the product labels of these EPs be amended to include the proposed new crop uses. The petitioner is proposing to add the following crops to the Sandea® Herbicide label: apple, bushberry Subgroup 13 - 07B, okra, succulent shelled pea and bean Subgroup 6B, dried shelled pea and bean (except soy bean) Subgroup 6C, rhubarb, and tuberous and corm vegetables Subgroup 1C. The petitioner is also proposing to amend the product label for GWN - 3061 Herbici de to add uses on dried shell pea and bean (except soy bean) Subgroup 6C . T he proposed use pattern information is presented in Table 3. Supplemental labels (dated 4/13/ 20 09) for both EPs were provided, along with a copy of the current accepted master labe l for Sandea® Herbicide, (undated). In addition, a description of the proposed uses corresponding to Section B for both EPs w as also included in the submission.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 10 of 34 Table 3 . Summary of Directions for Use of Halo sulfuron - Methyl . Applic. Timing, Ty pe, and Equ ip. Formulation

[EPA Reg. No.] Applic.

Rate (lb ai/A) Max. No.

Applic. per Season Max. Seasonal

Applic. Rate (lb ai/A) PHI

(days) Use Directions and

Limitations Apple; East of the Rocky Mts. Broadcast to orchard floor; G round ( ≥15 gal/A) 75% WG

[81880 - 18] 0.023 -

0.047 Not

specified (NS) 0.0 94 14 S ingle or sequential applications may be made on each side of the tree row . Use of a non - ionic surfactant (NIS) is recommended. Application to trees established less than one year is p rohibited. Apple; West of the Rocky Mts. Broadca st to orchard floor; G round ( ≥15 gal/A) 75% WG

[81880 - 18] 0.035 -

0.094 NS 0.094 14 S ingle or sequential applications may be made on each side of the tree row . Use of an NIS or a penetrating type surfactant is recommended. Application to trees established less than one year is prohibited. Bushberry Subgroup 13 - 07B

Soil broadcast ; G round ( ≥15 gal/A) 75% WG

[81880 - 18] 0.023 -

0.047 NS 0.094 14 Single or sequential applications may be made on each side of the r ow with a minimum retreatment interval ( RTI ) of 45 days for sequential applications. Use of an NIS is recommended. Application to plants established less than one year is prohibited. Fruiting Vegetables Group I ncluding B ut N ot L imited to E ggplant, O kra, P epper , and T om ato Row middle/furrow applications ; G round ( ≥15 gal/A ; ≥20 gal/A for okra from Section B ) 75% WG

[81880 - 18] 0.023 -

0.047 NS 0.094 30 Applications are to be made between rows of direct - seeded or transplanted fruiting vegetables . Pea and Bean, Succulent Shelled , Subgroup 6B 1 [ Any succulent shelled c ultivar of bean (Phaseolus, spp.), or immature soybean seed (Glycine max), or any Vigna spp., and garden pea (Pisum, spp.)] Preemergence; S oil broadcast; G round ( ≥15 gal/A) 75% WG

[81880 - 18] 0.023 1 0.023 30 Timing is after planting but before crop emerg ence.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 11 of 34 Table 3 . Summary of Directions for Use of Halo sulfuron - Methyl . Applic. Timing, Ty pe, and Equ ip. Formulation

[EPA Reg. No.] Applic.

Rate (lb ai/A) Max. No.

Applic. per Season Max. Seasonal

Applic. Rate (lb ai/A) PHI

(days) Use Directions and

Limitations Pea and Bean (Except Soybean) , Dried Shelled , Subgroup 6C 1 ; E ast of the Rocky Mts. Postemergence ; B roadcast or directed; G round ( ≥15 gal/A) 75% WG

[81880 - 2] [81880 - 18] 0.023 -

0.031 1 0.047 (per crop cycle) 0.094 (per year) 30 Application is to be m ade when plants have 2 to 4 trifoliate leaves, but before flow ering. An NIS is to be used. Directed sprays are recommended. Pea and Bean (Except Soybean) , Dried Shelled , Subgroup 6C ; West of the Rocky Mts. Postemergence ; B roadcast; G round ( ≥15 gal/A) 7 5% WG

[81880 - 2] [81880 - 18] 0.023 -

0.0 47 1 0.0 47 (per crop cycle) 0.0 94 (per year) 30 Application is to be made when plants have 2 to 4 trifoliate leaves, but before flow ering. An NIS is to be used. Directed sprays are recommended. Rhubarb Dormant ; B road cast; G round ( ≥15 gal/A) 75% WG

[81880 - 18] 0.023 -

0.047 1 0.047 60 Application is to be made as close as possible to breaking of dormancy. An NIS is to be used if labeled w eeds have emerged. Tuberous and Corm Vegetables, Subgroup 1C [Arracacha; arrow

root; artichoke, C hinese; artichoke, Jerusalem; canna, edible; cassava, bitter and sweet; chayote (root); chufa; dasheen (taro); ginger; leren; potato; sw eet potato; tanier; turmeric; yam bean; yam, true] Preemergence; Soil broadcast; Ground ( ≥15 gal/A) 75% WG

[81880 - 18] 0.023 -

0.047 2 0.047 45 First application is to be made after planting but prior to crop emergence; if necessary, a second application may be made 45 days before harvest. If a second application is made, an NIS should be used in the second application. Po stemergence Foliar broadcast Ground ( ≥15 gal/A) 1 Individual crop uses of Sandea® Herbicide (EPA Reg. No. 81880 - 18) are currently registered on succulent beans and dry beans ; the petitioner now requests uses on Subgroups 6B and 6C . The EP, GWN - 3061 Herbicide (EPA Reg. No. 81880 - 2), is also currently registered on soybeans. The master label for Sandea® Herbicide includes the following additional directions: (1) ground applications are to be made in a minimum of 15 gal/A of water; (2) air assisted (airblast) field crop sprayers are p rohibited; and (3) application through any ty pe of irrigation sy stem is prohibited. The label also includes the following statement pertaining to adjuvant use: “Unless otherwise stated, a nonionic surfactant (NI S) is recommended in the spray solution for postemergence applications or for preemergence applications where susceptible weeds are present prior to crop emergence.” Plantback restrictions are also specified on the master label for a number of crops, ranging from 0 months for sugarcane and insecti cide - /imidazolidone - resistant field corn to 36 months for sugarHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 12 of 34 beet in N D, MN, and the Red River Valley , strawberries (6 months for annual FL transplants), and crops not specifically listed. HED previously

determined that rotational crop tolerances/restrictions are not needed for halosulfuron - methyl. The restrictions appear to have been established for protection of the rotated crops from residual herbicidal activity . Conclusions . The submitted labels for Sandea® Herbicide (EPA Reg. No. 81880 - 18) and GWN 3061 Herbicide (EPA Reg. No. 81880 - 2) are adequate to allow evaluation of the residue data relative to the proposed use s . However, the petitioner is required to i) amend the proposed use directions of Sandea® Herbicide (EPA Reg. No. 81880 - 18) on Crop Subgroup 6B to prohibit applications to legumes grown for livestock feeds because no residue data are available for cowpea forage and hay ; ii) amend the proposed use directions of Sandea® Herbicide (EPA Reg. No. 81880 - 18) on Crop Subgroup 13 - 07B (bushberry ) to remove the instructions pertaining to the use of a non - ionic surfactant; iii) remove the use directions from both labels for Crop Subgroup 6C (dried pea and bean (except soy bean)) . Additional recommendations pertaining to label amendments may

be found in the respective ‘Magnitude of the Residue’ section and summarized in the ‘L ist of Deficiency ’ section . 860.1300 Nature of the Residue - Plants DP#251007, M. Doherty, 12/10/ 19 98 Metabolism Committee decision, G . Herndon , 5/21/ 19 96 DP#198361 , G. Otakie , 7/21/ 19 94 DP#s173627 & 180565, G. Herndon , 7/30/ 19 92 The nature of the residue in plants is adequately understood based on acceptable metabolism studies reflecting pre - and postemergence modes of applications on corn, sugarcane, and soy bean. The metabo lism of halosulfuron - methyl was similar in the three tested crops but dependent on the mode of application. When halosulfuron - methyl was applied preemergence, initial breakdown of the herbicide in the soil and preferential uptake of the py razole moieties resulted in the primary

residue being 3 - CSA, which has been determined to be less toxic than the parent. With a postemergence application, the major residue was the parent compound with minimal translocation of the herbicide in the plant, except in grain where the major residue was 3 - CSA. Based on the very

low toxicity

of the metabolite 3 - CSA, relatively low toxicity

of the parent compound, and low residue levels of both parent compound and the 3 - CSA metabolite, HED has previously

d etermined that the residue of concern in plants is the parent compound, halosulfuron methyl. 860.1300 Nature of the Residue - Livestock DP#223801, 11/17/ 19 98, M. Doherty Metabolism Committee decision, G . Herndon , 5/21/ 19 96 DP#204062, G. Herndon , 6/22/199 4 DP#184435, G. Herndon , 1/15/1993 DP#181023, G. Herndon , 11/12/1992 DP#s173627 & 180565, G. Herndon , 7/30/1992Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 13 of 34 An a cceptable goat metabolism study w as previously submitted and reviewed in conjunction with petitions for uses on corn and sorghum. In goat milk and tissues, the major extractable residue was the parent; acid hydroly sis released bound or conjugated residues of aminopy rimidine and 3 - CSA. HED has previously determined that the residue of concern in ruminants is halosulfuron methyl; however, be cause the approved enforcement method for livestock commodities quantifies the parent compound and metabolites containing the 3 - CSA moiety by converting residues to 3 - CSA, tolerances for residues in livestock commodities are expressed in terms of halosulfuron - methyl and its metabolites determined as 3 - CSA, expressed as halosulfuron - methyl equivalents. There are no poultry f

eedstuffs associated with the recommended tolerances and crop us es addressed in this action. Therefore, a discussion of the metaboli sm of halosulfuron - methyl in poultry is not germane to this petition. 860.1340 Residue Analytical Methods DP#250584, G. Herndon , 10/28/1998 DP#214890, G. Herndon , 5/3/1995 DP#202131, G. Herndon , 10/4/1994 Plants Enforcement method: An adequate analy tical method is available for enforcement of tolerances for halosulfuron - methyl residues in plants. The GC method quantifies halosulfuron - methyl as its rearrangement ester (1 -H - py razole - 4 - carboxylic acid, 3 - chloro - 5 - [(4,6 - dimethoxy- 2 - py rimidinyl)amino] - 1 - methyl, methyl ester) using thermionic - specific detection (TSD, nitrogen specific). Monsanto Analy tical Method RES - 109 - 97 - 4 (MRID 44495801) has been validated as an enforcement method by the Analy

tical Chemistry

Branch (ACB)/BEAD. The LOQ on rice straw, sugarcane, milo grain, field corn grain, cotton gin by products, and almond nutmeats was estimated to be 0.05 ppm (DP#250584, G. Herndon, 10/28/ 19 98).

N N O C H 3

O C H 3 N H N N C H 3 Cl O O

C H 3

Rearrangement ester (RRE) of halosulfuron - methyl Data collection method

s : Samples collected from the field trial and process ing studies associated with this action were analy zed for residues of halosulfuron - methyl using the available tolerance enforcement method, Method RES - 109 - 97 - 4, with minor modifications. Briefly , samples were extracted with aceto nitrile (ACN)/water, filtered, and partitioned with dichloromethane (DCM). The DCM extract was evaporated to dry ness and redissolved in 15% methanol/DCM for clean - up through a Florisil solid phase extraction (SPE) cartridge. The eluate was mixed with 0.5 M potassium carbonate to convert halosulfuron - methyl residues to the RRE. The reaction mixture was then extracted with DCM, and the DCM extract was evaporated toHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 14 of 34 dry ness; residues were reconstituted in ethyl acetate for further clean - up through a silica SPE column. The eluate was evaporated to dry ness and redissolved in 50% ethyl acetate/isooctane for analy sis by

gas chromatography

with nitrogen phosphorus detection (GC/NPD) . Residues were expressed in terms of halosulfuron - methyl. The GC/ N PD method wa s adequate for data collection based on acceptable method validation and concurrent method recoveries. The LLM V was 0.0 5 ppm . Conclusions . The residue analy tical methods data are adequate to satisfy data requirements for the subject action. An a cceptab le residue analy tical method is available for tolerance enforcement purposes for residues in/on crop commodities . R esidues of halosulfuron - methyl in/on the crop commodities from the magnitude of the residue studies were determined using an acceptable data collection method. Li vestock Enforcement method: An adequate analy tical method is available for enforcement of tolerances for secondary

residues of halosulfuron - methyl in livestock commodities. Monsanto Analy tical Method RES - 046 - 93 quantifies halosulf uron - methyl and metabolites containing the 3 - CSA moiety , expressed as parent equivalents. Residues of halosulfuron - methyl and 3 - chlorosulfonamide ester are hydroly zed to 3 - CSA, which is extracted with ACN/DCM and then methylated with trimethylsilyl - diazom ethane. The methyl ester is analy zed by GC with electron capture detection (ECD) after cleanup with an alumina/carbon column. The petitioner - validated LOQ was 0.01 ppm . The method has been validated as an enforcement method by the Analy

tical Chemistry

B ranch (ACB)/BEAD at an LOQ of 0.01 ppm in milk and liver (D. Swineford, 4/28/ 19 95) . 860.1360 Multiresidue Methods DP# 189198, G.Herndon , 3/8/ 19 94 Adequate multiresidue method data for halosulfuron - methyl and 3 - CSA were submitted previously

in conjunctio n with PP# 3F4193 . Residues of halosulfuron - methyl and 3 - CSA are not recoverable by

the FDA Multiresidue Protocols A through E. The results have been forwarded to FDA. 860.1380 Storage Stability The storage durations and conditions of crop samples from the submitted magnitude of the residue and processing studies are presented in Table 4.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 15 of 34 Table 4. Sum ma ry of Storage Conditions and Durations of Sam ples fromCrop Field Trials. Matrix Storage

Tem perature (°C) Actual Storage

Duration Interval of Demo nstrated

Storage Stability for Halosulfuron - methyl 1 Apple fruit ≤ - 4 at the field sites ≤ - 8 at the analytical facility 78 - 110 days

(2.6 - 3.6 months) Up to 104 days (3.4 months) in/on frozen apple

fruit Blueberry fruit ≤ - 2 at the field sites ≤ - 20 at the analytical facility 76 - 125 days

(2.5 - 4.1 months) Up to 146 or 175 days (4.8 or 5.7 months) in/on

frozen blueberry fruit Dry bean seed ≤ - 10 at the field sites ≤ - 12 at the analytical facility 293 - 328 days

(9.6 - 10.8 months) Up to 326 days (10.7 months) in/on frozen bean

seed Succulent pea seed ≤ - 10 at the field sites (on blue ice at the GA site) ≤ - 20 at the analytical facility 64 - 222 days

(2.1 - 7.3 months) Up to 242 days (8.0 months) in/on frozen pea seed

Potato tuber ≤ - 2 at the field sites ≤ - 20 at the analyt ical facility 114 - 279 days

(3.7 - 9.2 months) Up to 284 days (9.3 months) in/on frozen potato

tuber Potato tuber (RAC) ≤ - 20 at the analytical facility 246 days

(8.1 months) Up to 284 days (9.3 months), 302 days (9.9

months), 297 days (9.8 months), and 288 d ays (9.5 months) in/on frozen potato tuber, flakes/granules, chips, and wet peel, respectively Potato granules/flakes Shipped directly to processor at ambient temperature ≤ - 12 at the processing facility ≤ - 20 at the analytical facility 296 - 300 days

(9.7 - 9. 9 months) Potato chips 292 days (9.6 months) Potato wet peel 244 - 251 days (8.0 - 8.2 months) Rhubarb petiole ≤ - 5 at the field sites < - 20 at the analytical facility 113 - 165 days

(3.7 - 5.4 months) Up to 169 or 233 days (5.6 or 7.7 months) in/on

frozen r hubarb petiole 1 Storage stability determined from concurrent field trial samples. To support the current apple, blueberry , dry bean, succulent pea, potato, and rhubarb field trial and potato processing data, storage stability studies were conducted in conjunction with the field trials and processing study . For each crop, control samples of the respective matrices were fortified with halosulfuron - methyl at 0.5 ppm and placed in storage under the same frozen c onditions as the treated samples. No zero - day analy ses were conducted on the fortified samples placed into storage. Rather, triplicate stored samples were analy zed along with a control sample and freshly

fortified samples at an interval reflecting the maximum storage intervals from the field trials . Average corrected recoveries of halosulfuron - methyl f ollowing frozen storage were 96 % from apple after 104 day s , 93 % for blueberry after 175 day s , 95 % from dry bean seed after 326 day s, 102 % for succulent pea seed after 242 day s, 99% from potato tuber a fter 284 day s, 98 - 115% from potato processed commodities after 288 - 302 day s, and 90% from rhubarb after 233 day s . Although no 0 - day analy sis was conducted, the data indicate that halosulfuro - methyl is stable under frozen storage conditions for up to 3. 4 m onths in apple, 5.7 months in blueberry , 10.7 months in dry

bean seed, 8.0 months in succulent pea seed, 9.3 months in potato tuber, 9.5 - 9.9 months in potato processed commodities, and 7.7 months in rhubarb . Conclusions . A dequate storage stability data are available to support the storage conditions and durations of samples collected from the magnitude of the residue and processing studies on apples, blueberry , dry

bean seed, succulent pea seed, potato tuber, potato processed commodities,Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 16 of 34 and rhubarb. As residues of halosulfuron - methyl were found stable in tested crop matrices, storage stability

corrections need not be applied to the recommended tolerances for halosulfuron methyl residues for these commodities . 860.1400 Water, Fish, and Irrigated Crops There are no proposed uses that are relevant to this guideline topic. 860.1460 Food Handling There are no proposed uses that are relevant to this guideline topic. 860.1480 Meat, Milk, Poultry, and Eggs DP# s 189198 & 198051 , G. Herndon , 3/8/ 19 94 DP#s173 627 & 180565, G. Herndon , 7/30/1992 The livestock feedstuffs associated with the proposed uses are wet apple pomace and potato culls and processed waste. The feedstuffs derived from registered uses include those commodities derived from alfalfa, almond, corn, c otton, dry and snap beans, rice, sorghum, soy bean , and sugarcane. The dietary

burdens of halosulfuron - methyl to beef and dairy cattle resulting from the proposed and registered use s are presented in Table 5 a . There are no poultry and swine feedstuffs associated with the proposed uses. T he dietary burdens were re - calculated according to the Agency

guidance on constructing maximum reasonably balanced diets (June 30, 2008) and used the proposed and existing tolerances for feedstuffs. The calculated dietary burdens are 0. 468 ppm for beef cattle and 0. 825 ppm for dairy cattle. Table 5 a . Calculation of Dietary Burdens of Halosulfuron - me thyl Residues to Livestock. Feedstuff Ty pe 1 % Dry Matter2 % Diet2 Recommended Tolerance (ppm) Dietary Contributio n (ppm) 3 Beef Cattle Alfalfa, hay R 89 15 2.0 0.337 Potato, processed w aste CC 15 30 0.05 0.100 Corn, field, grain CC 88 50 0.05 0.028 Soybean, meal PC 92 5 0.05 0.003 TOTAL BURDEN -- -- 100 -- 0.468 Dairy Cattle Alfalfa, forage R 35 20 1.0 0.571 Corn, field, stover R 83 15 0.80 0.145 Corn, field, forage R 40 10 0.20 0.050 Potato, processed w aste CC 15 10 0.05 0.033 Corn, field, grain CC 88 35 0.05 0.020 Cotton, meal PC 89 10 0.05 0.006 TOTAL BURDEN -- -- 100 -- 0.825 1 R: Roughage; CC: Carbohydrate concentrate; PC: Protein concentrate. 2 OPPTS 860.1000 Table 1 Feedstuffs ( June 2008). 3 Contribution = ([tolerance /% DM] X % diet) for beef and dairy cattle; contribution = ([tolerance] X % diet) for poultry and swine.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 17 of 34 An adequate dairy

c attle feeding study

was reported in PP#3F4193 (DP#s 189198 and 198051, G. Herndon, 3/8/ 19 94). Halosulfuron - methyl (MON 1200) was administered in gelatin capsules to lactating dairy

cattle (four animals/dose group) once daily for 28 c onsecutive day s at 3 dose levels (roughly

equivalent to 0.5, 1.5, and 5 pp m in the daily diet on a dry

weight basis). Four control animals were given untreated capsules. Milk samples were collected from each a.m. and p.m. milking from Day

1 until the day of sacrifice. Within 12 hours after the last dose of test material, the animals were sacrificed , and samples of liver, kidney , fat, and muscle were collected, finely

ground, and frozen until analy sis. The samples were analy zed either by

Method RES - 021 - 9 2 (milk samples) or Method RES - 027 - 92 (meat matrices). B oth methods convert hal osulfuron - methyl ( MON 12000 ) , MON 12000 acid, des - methyl MON 12000, and chlorosulfonamide ester to a single chemophore, chlorosulfonamide acid. Prior to sample analy sis, the p erformance of the methods was tested using both unlabeled MON 12000 fortifications as well as the radiolabeled goat milk and liver samples obtained from the carbon - 14 goat metabolism study . Adequate storage stability of MON 12000 in the various matrices w as shown to cover the storage interval of the samples. No residues were detected in the controls above the 0.01 ppm detection limit. T he results of the cattle feeding study are shown in Table 5b. Table 5b. Maxim um Residues in Dairy Cattle Tissues and Milk . Dose (ppm) Maximum Residue (ppm) 1

Whole Milk Raw Cream Raw Skim Milk Muscle Fat Liver Kidney 0.5 NA 2 NA NA NA NA 0.01 0.02 1.5 NA NA NA <0.01 <0.01 0.04 0.11 5.0 <0.01 <0.01 <0.01 <0.01 <0.01 0.11 0.24 1 Total CSA, expressed as MON 12000 equivalents . 2 NA

– not analyzed . No detectable residues (<0.01 ppm) were found in milk, muscle, and fat of cattle at feeding levels of 0.5, 1.5, and 5.0 ppm. Detectable residues were found in liver and kidney at all feeding levels. Conclusion s . T he livestock feedstuffs derived from registered and proposed uses w ould not significantly

increase the dietary

burden s of halosulfuron - methyl to beef and dairy cattle p rovided the petitioner amends the proposed use directions of Sandea® Her bicide on Crop Subgroup 6B to prohibit applications to legumes grown for livestock feeds. The available dairy cattle feeding study is adequate, and ARIA continues to conclude that tolerances for halosulfuron - methyl residues of concern need not be establis hed for the milk , meat , and fat of cattle, goat, hog, horse, and sheep. The established tolerance of 0.1 ppm for the meat by products of cattle, goat, hog, horse, and sheep remain adequate. There are no poultry and swine feedstuffs associated with the rec ommended tolerances and crop uses . The petitioner should note that if additional uses are proposed in the future which would result in an increase in the dietary burden s , ARIA/HED will re - assess the adequacy

of established animal tolerances.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 18 of 34 860.1500 Cro p Field Trials DER References: 47772101.der.doc (Succulent Pea)

47772102.de1.doc (Potato) 477 72103 .der.doc ( Rhubarb ) 477 72104 .der.doc ( Blueberry) 477 72105 .de r .doc ( Dry Bean ) 477 72106 .de r .doc ( Apple ) IR - 4 has submitted magnitude of the residue stu dies on apples, blueberry , dry bean, succulent pea, potato, and rhubarb. The results from these field trials are discussed below and the residue data are summarized in Table 6 . As all residues in/on treated commodity samples were be low the LLM V (<0.05 ppm) when the test formulation was applied to the crops according to the conditions and parameters used in the field trials, the Agency ’s tolerance spreadsheet was not used for tolerance assessments and recommendations. Table 6 . Sum m ary of Residue Data fromCrop Field Trials with Halosulfuron - me thyl. Crop Matrix Total Applic.

Rate (lb ai/A) PHI

(days) Residues of Halosulfuron - methyl (ppm)

n Min. Max. HAFT 1 Median Mean Std. Dev. Apple (proposed use = 0.094 lb ai/A total applicati on rate, 14 - day PHI) Apple ( fruit ) 0.092 - 0.104 13 - 14 26 <0.05 <0.05 <0.05 0.05 0.05 -- Bushberry Subgroup 13 - 07B (proposed use = 0.094 lb ai/A total application rate, 14 - day PHI) Blueberry ( fruit ) 0.093 - 0.099 13 - 14 12 <0.05 <0.05 <0.05 0.05 0.05 -- O kr a (proposed use = 0.094 lb ai/A total application rate, 30 - day PHI) Okra No okra data w ere submitted. Pea and Bean, Succulent Shelled, Subgroup 6B (proposed use = 0.023 lb ai/A total application rate, 30 - day PHI) Pea seed 0.032 55 - 68 4 <0.05 <0.05 <0.0 5 0.05 0.05 --

0.060 - 0.070 55 - 72;

166 2 18 <0.05 <0.05 <0.05 0.05 0.05 -- Pea seed in pods 0.065 - 0.066 69 - 77 6 <0.05 <0.05 <0.05 0.05 0.05 -- Pea and Bean (Except Soybean), Dried Shelled, Subgroup 6C (proposed use = 0.047 lb ai/A total application rate per crop cycle and 0.094 lb ai/A total application rate per year, 30 - day PHI) Dry bean seed 0.061 - 0.075 27 - 31 24 <0.05 <0.05 <0.05 0.05 0.05 -- Rhubarb (proposed use = 0.047 lb ai/A total application rate, 60 - day PHI) Rhubarb petiole 0.093 - 0.101 61 - 78 8 <0.05 <0.05 <0.05 0.05 0.05 -- Tuberous and CormVegetables, Subgroup 1C (proposed use = 0.047 lb ai/A total application rate, 45 - day PHI) Potato tuber 0.094 - 0.103 42 - 46 28 <0.05 <0.05 <0.05 0.05 0.05 -- 1 HAFT = highest average field trial result. 2 Includes one trial (2 samples) harvested at a 166 - day PHI.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 19 of 34 Apple IR - 4 has submitted field trial data for halosulfuron - methyl with apple from 13 field trials conducted in the United States in Zones 1 (NY; 3 trials), 2 (NJ, NC; 2 trials), 5 (MI ; 2 trials), 9 (CO; 1 trial), 10 (CA; 1 trial), and 11 (ID, WA; 4 trials) during the 2006 growing season. At each trial site, two broadcast applications of a 75% WG formulation of halosulfuron - methyl were made to the orchard floor during the fruiting growth stages, at 0.044 - 0.053 lb ai/A/application, with a 13 - to 15 - day

retreatment interval (RTI ) , for a total rate of 0.092 - 0.104 lb ai/A (~ 1X the proposed maximum seasonal rate). Applications were made using ground equipment in spray volumes of 15 - 36 gal/A, without an adjuvant. Samples of commercially mature apple fruit were collected at a 13 - to 14 - day PHI . An additional plot was established at the NJ site using a total seasonal rate of 0.484 lb ai/A, to generate samples for processing; however, as residues were non detectable in any

apple fruit sample, processing was not initiated. Samples of apple fruit were analy zed for residues of halosulfuron - methyl as its rearrangement ester using the available tolerance enforcement method , Method RES - 109 - 97 - 4, with modificatio ns. The gas chromatography method with nitrogen - phosphorus detection (GC/NPD) is adequate for data collection based on acceptable method validation and concurrent method reco veries. The LLMV for halosulfuron - methyl in apple was 0.05 ppm . The maximum sto rage duration for apple fruit samples was 110 day s (3.6 months). To support sample storage conditions and durations, storage stability data were generated concurrently with the field trial study . These data demonstrate that residues of halosulfuron - methyl are stable in/on fortified apple fruit stored frozen for up to 104 day s (3.4 months). Residues of halosulfuron - methyl were below the LLMV (<0.05 ppm) in/on all samples of apple fruit harvested 13 or 14 day s following the second of two broadcast applicat ions of the 75% WG formulation of halosulfuron - methyl at a total seasonal rate of 0.092 - 0.104 lb ai/A. Conclusions : The submitted field trial data for halosulfuron - methyl on apples are adequate with regard to the number and location of field trials . T he application rate and PHI reflect the proposed use pattern, and the data are supported by concurrent storage stability data. Although the apple data d id not reflect the use of a nonionic surfactant as recommended on the proposed label , this is not an issu e as the application is directed to the orchard floor and presence/absence of surfactant is not expected to change the residue level on the apple fruit. The available data will support the proposed tolerance of 0.05 ppm for appl e.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 20 of 34 Bushberry

Subgroup 13 - 07B IR - 4 has submitted field trial data for halosulfuron - methyl with blueberry as a representative of the Crop Subgroup 13 - 07B , bushberry . Six blueberry trials were conducted in the United States in Zones 1 (ME; 1 trial), 2 (NJ and NC; 2 trials), 5 (MI ; 2 trials), and 12 (OR; 1 trial), during the 2006 growing season. At each trial location, a single soil broadcast application of a 75% WG formulation of halosulfuron - methyl was made during the crops’ fruiting growth stage at a rate of 0.093 - 0.099 lb ai/A (~ 1X the proposed maximum rate). Applications were made to either side of each plant row using ground equipment in spray volumes of ~16 - 23 gal/A except for the OR trial where a spray

volume of 62 gal/A was used; no adjuvant was included in any of the spray volumes. Samples of commercially mature blueberry

fruit were collected at a 13 - or 14 - day PHI . Samples of blueberry

fruit were analy

zed for residues of halosulfuron - methyl as its rearrangement ester using the available tolerance enforcement method , Method RES - 109 - 97 - 4, with modifications. The GC/NPD is adequate for data collection based on acceptable method validation and concurrent method recoveries. The LLMV for halosulfuron - methyl in blueberry fruit was 0.0 5 ppm . The maximum storage duration for b lueberry samples was 125 day s (4.1 months). To support sample storage conditions and durations, storage stability study data were generated concurrently with the field trial study . These data demonstrate that residues of halosulfuron - methyl are stable in/on fortified blueberry

fruit stored frozen for up to 175 day s (5.7 months). Residues of halosulfuron - methyl were below the LLMV (<0.05 ppm) in/on all samples of blueberry harvested 13 or 14 day s following a single soil broadcast application of the 75% WG formulation of halosulfuron - methyl at 0.093 - 0.099 lb ai/A. Conclusions : The submitted field trial data for halosulfuron - methyl on blueberries , the representative commodity of Crop Subgroup 13 - 07B, are adequate with regard to the number and location of f

ield trials . Although the number of field trials is a 25% reduction of the OPPTS 860.1500 guidance, this number is considered sufficient, for halosulfuron - methyl, to support the S ubgroup 13 - 07B tolerance based on the lack of quantifiable residues. T he ap plication rate and PHIreflect the proposed use pattern, and the data are supported by concurrent storage stability data. However, the blueberry data d id not reflect the use of a nonionic surfactant as recommended on the proposed label. The b lue berr y dat a will support and ARIA recommends for the proposed tolerance of 0.05 ppm for the b ushberry Subgroup 13 - 07B provided the label for Sandea® Herbicide is amended to remove the instructions pertaining to the use of a non - ionic surfactant on crops belonging to the Subgroup 13 - 07B. I f it is IR - 4’s intention to add a nonionic surfactant when Sandea® Herbicide is applied on Subgroup 13 - 07B, then additional field trial data are required. Although the spray is directed to the rows between bluebe r ry bushes, there i s a finite possibility

of the spray

contacting the bushes, and the presence/absence of surfactant might impact the residue on the blueberries.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 21 of 34 Okra DP#267423, A. Acierto , 4/25/2002 No residue data were submitted to support the proposed use on okra. Okr a was listed by the petitioner in its proposed labels as part of the fruiting vegetables crop group . The ChemSAC meeting of 10/18/ 20 06 has recommended the inclusion of okra in Crop Group 8 ( fruiting vegetables ). The ChemSAC has also determined that a sep arate tolerance for okra should be listed in the appropriate section of the CFR entry until the new crop group regulation is published. A tolerance of 0.05 ppm for residues of halosulfuron - methyl has been established on the fruiting vegetable Crop Group 8 based on field trial data for tomato and pepper (DP#267423, A. Acierto , 4/25/ 20 02 ). The available field trial data for fruiting vegetables will be translated to okra. ARIA recommend s for the establishment of a tolerance of 0. 05 ppm for residues of halos ulfuron - methyl in/on okra . This recommendation is identical to the level proposed by the petitioner. Pea and Bean, Succulent Shelled, Subgroup 6B DP#278587, A. Acierto , 6/15/2002 IR - 4 has submitted field trial data for halosulfuron - methyl on succulent shelled and edible podded peas from 12 field trials conducted in the United States during the 2003 - 2004 growing seasons. Nine trials on succulent shelled peas were conducted in Zones 2 (GA and SC; 2 trials), 5 (OH and WI ; 4 trials), 11 (WA; 2 trials), and 12 (OR; 1 trial). Three trials on edible podded pea were conducted in Zones 1 (NY; 1 trial) and 10 (CA; 2 trials). Each trial site consisted of one untreated plot and two treated plots. Each treated plot received a single postplant p reemergence broadca st soil application of a 75% WG formulation of halosulfuron - methyl at ~0.032 lb ai/A (Treatment Plot 2 ; ~1. 4X the maximum proposed rate ) or ~0.064 lb ai/A (Treatment Plot 3 ; ~2. 8X ). All applications were made using ground equipment in 20 - 38 GPA spray volumes, without an adjuvant. Samples of commercially mature pea seed were collected at a 55 - to 77 - day

PHI ; however, at one trial, peas were collected at a 166 - day PHI . Samples of succulent pea seed, with and without pods, were analy zed for residues of halo sulfuron - methyl as its RRE using the available tolerance enforcement method , Method RES 109 - 97 - 4, with modifications. The GC/NPD is adequate for data collection based on acceptable method validation and concurrent method recoveries. The LLMV for halosulf uron - methyl was 0.0 5 ppm. The maximum storage duration for pea seed samples was 222 day s (7.3 months). To support sample storage conditions and durations, a concurrent storage stability study was conducted with the field trial study . These data demonstr ate that residues of halosulfuron - methyl are stable in/on fortified pea seed stored frozen for up to 242 day s (8.0 months). Residues of halosulfuron - methyl were below the LLMV (<0.05 ppm) in/on all samples of peas ( succulent shelled and edible podded) h arvested 55 - 166 day s following a single preemergence broadcast application of the 75% WG formulation of halosulfuron - methyl, made to the soil at aHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 22 of 34 rate of 0.060 - 0.070 lb ai/A (Treatment Plot 3). Residues were also below the L LM V (<0.05 ppm in/on samples of pea seeds treated at 0.032 lb ai/A (Treatment Plot 2). Vary ing degrees of phy totoxicity were reported at all but three of the test sites. The petitioner reported phy totoxic effects resulting in plant stunting/thinning or chlorosis at the NY, OH, SC, W I, and WA trial sites, and one CA trial site. No phy totoxic effects were noted at the three remaining trials. Although phy

totoxicity appears to be attributed to the test substance application, these instances of phy totoxicity did not have an adverse impa ct on the residue trials. Conclusions : The representative crops of Subgroup 6B are two commodities of: (1) any succulent shelled cultivar of bean ( Phaseolus spp.) or (2) immature soy bean seed ( Glycine max ) or (3) any Vigna spp. and garden pea ( Pisum spp. ). The submitted field trial data for succulent peas do not fully

support the proposed use pattern because the trials were conducted at exaggerated rates (1. 4 X or 2. 8X ) and the collected samples d id not reflect the proposed 30 - day PHI(the earliest PHI

te sted was 55 day s). The available data for succulent beans, previously submitted under PP#1E06322 (DP#278587, A. Acierto , 6/15/ 20 02 ) to support the established individual tolerance of 0.05 ppm , also do not reflect the proposed use on Subgroup 6B because th ese data represent foliar application whereas the new proposed use pattern is for preemergence soil application. ARIA will not require additional data on succulent peas since treatment at 1X will likely result in residues below 0.05 ppm , even when harve sted at a PHIof 30 - day s . ARIA will also not require additional data on succulent beans since soil treatment will likely result in residues below 0.05 ppm. ARIA recommends for the proposed tolerance of 0.05 ppm for the Subgroup 6B (p ea and b ean , s ucculent s helled ) . Concomitant with the establishment of a tolerance for Subgroup 6 B, the individual tolerance for ‘bean, snap , succulent ’ should be revoked . Pea and Bean (Except Soy bean), Dried Shelled, Subgroup 6C DP# 278587, A. Acierto , 6/15/2002 IR - 4 has submitted field trial data for halosulfuron - methyl with dry bean as a representative of the Crop Subgroup 6C dried s helled b ean ( e xcept s oy bean ) and p ea . Twelve field trials were conducted in the United States with dry bean in Zones 1 (NY; 1 trial), 5 (N D, SD, and WI ; 5 trials), 7 (NE and ND; 2 trials), 8 or 9 (CO; 2 trials), 10 (CA; 1 trial), and 11 (WA; 1 trial) during the 2005 growing season. At each trial site, a single foliar broadcast postemergence application of a 75% WG formulation of halosulfuro n - methyl was made during the crop’s blooming or fruiting growth stage at 0.061 - 0.075 lb ai/A (~ 1.3 - 1. 6 X the proposed application rate per crop cycle and ~ 0.6 - 0. 8 X the proposed total application rate per year) . Applications were made using ground equipment in spray volumes of ~18 - 35 gal/A; an NI S was added as an adjuvant. Samples of commercially

mature dry

bean seed were collected at a 27 - to 31 - day PHI . Samples of dry

bean seed were analy

zed for residues of halosulfuron - methyl as its RRE using the availa ble tolerance enforcement method , Method RES - 109 - 97 - 4, with modifications. The GC/NPD is adequate for data collection based on acceptable method validation and concurrent method recoveries. The LLMV for halosulfuron - methyl in dry bean seed was 0.0 5 ppm . The maximum storage duration for dry bean seed samples was 328 day s (10.8 months). To support sample storage conditions and durations, storage stability study data were generatedHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 23 of 34 concurrently

with the field trial study . These data demonstrate that resid ues of halosulfuron methyl are stable in/on fortified dry bean seed stored frozen for up to 326 day s (10.7 months). Residues of halosulfuron - methyl were below the LLMV (<0.05 ppm) in/on all samples of dry bean seed harvested 27 to 31 day s following a sing le foliar broadcast postemergence application of the 75% WG formulation of halosulfuron - methyl at 0.061 - 0.075 lb ai/A. Conclusions : The representative c ommodities of Subgroup 6C are any one dried cultivar of bean ( Phaseolus spp.) and any

one dried cultiv ar of pea ( Pisum spp.) The submitted residue data for dry bean are adequate with regard to geographic representation of data ; the data are supported by concurrent storage stability data . The dry

bean data from the current submission reflect a single foli ar broadcast application conducted at ~1. 6 X the proposed application rate per crop cycle (or ~0. 8 X the proposed total application rate per year), the use of a nonionic surfactant, and the treated samples were collected approximating the proposed 30 - day PHI . Additional data for dry beans were submitted under PP#1E06322 (DP#278587, A. Acierto , 6/15/ 20 02 ) to support the established individual tolerance of 0.05 ppm. These data represent a single application of Permit 75 WG Herbicide at 0.032 lb ai/A made 0 to 6 day s after planting and a 86 - to 113 - day PHI . ARIA is unable to recommend for the proposed tolerance of 0.05 ppm for Crop Subgroup 6C ( Dried Shelled Bean (Except Soy bean) and Pea ) at this time because residue data on dried pea including the forages and hay of field pea cultivars are required. When adequate residue data for dried peas become available, the petitioner may again request a tolerance for Subgroup 6C . A revised Section F should be submitted removing the request for Crop Subgroup 6C (dried s helled pea and bean (except soy bean)). Rhubarb IR - 4 has submitted field trial data for halosulfuron - methyl on rhubarb from four field trials conducted in the United States in Zones 5 (MI ; 1 trial) and 12 (OR; 3 trials) during the 2006 growing season. At each trial location, a single soil broadcast application of a 75% WG formulation of halosulfuron - methyl was made at the end of plant dormancy , at a rate of 0.093 - 0.101 lb ai/A (~2.0 - 2. 1X the proposed rate) . Applications were made using ground equipment i n spray volumes of ~20 - 32 gal/A; an NI S was added as an adjuvant. Samples of rhubarb petiole (stalk plus leaf) were collected at a 61 - to 78 - day PHI . Samples of rhubarb petiole were analy zed for residues of halosulfuron - methyl as its RRE using the availa ble tolerance enforcement method , Method RES - 109 - 97 - 4, with modifications. The GC/NPD is adequate for data collection based on acceptable method validation and concurrent method recoveries. The LLMV for halosulfuron - methyl in rhubarb was 0.05 ppm . The m aximum storage duration for rhubarb petiole samples was 165 days (5.4 months). To support sample storage conditions and durations, a concurrent storage stability study was conducted with the field trial study . These data demonstrate that residues of halo sulfuron - methyl are stable in/on fortified rhubarb stored frozen for up to 233 day s (7 .7 months). Residues of halosulfuron - methyl were below the LLMV (<0.05 ppm) in/on all samples of rhubarb petiole harvested 61 to 78 day s following a single soil broadc ast application of the 75%Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 24 of 34 WG formulation of halosulfuron - methyl at 0.093 - 0.101 lb ai/A. Conclusions : The submitted field trial data for halosulfuron - methyl on rhubarb are adequate with regard to the number and location of field trials. The data also re flect the use of nonionic surfactant as recommended on the proposed label , samples were collected at appropriate PHI , and are supported by

concurrent storage stability data. However, the rhubarb data were generated using slightly

exaggerated rates of ~2.0 - 2. 1X . ARIA will not require additional data on rhubarb since treatment at 1X will likely result in residues below 0.05 ppm. The available data will support the proposed tolerance of 0.05 ppm for rhubarb. Tuberous and Corm Vegetables, Subgroup 1C IR - 4 has submitted field trial data for halosulfuron - methyl with potato as a representative of the Crop Subgroup 1C tuberous and corm vegetables . Fourteen potato trials were conducted in the United States in Zones 1 (ME and NY; 2 trials), 2 (NJ; 1 trial), 3 (F L; 1 trial), 5 (ND and WI ; 3 trials), 9 (CO; 1 trial), 10 (CA; 1 trial), and 11 (ID and WA; 5 trials), during the 2004 growing season. At each test location, two broadcast applications of a 75% WG formulation of halosulfuron - methyl were made at 0.046 - 0.05 2 lb ai/A/application for a total seasonal rate of 0.094 - 0.10 lb ai/A (~2.0 - 2. 1X the proposed maximum seasonal rate). The first application was made to bare soil; the second was made as a foliar application 27 to 96 day s later when the plants were in a ve getative to post bloom growth stage. Applications were made using ground equipment in spray

volumes of ~12 - 32 gal/A. The first application did not include an adjuvant, but the second included a non - ionic surfactant. Samples of commercially mature potato tuber were collected at a 42 - to 46 - day PHI . At one WA site, additional bulk samples of potato tuber were collected for processing. Samples of potato tuber were analy zed for residues of halosulfuron - methyl as its RRE using the available tolerance enforc ement method , Method RES - 109 - 97 - 4, with modifications. The GC/NPD is adequate for data collection based on acceptable method validation and concurrent method recoveries. The LLM V for halosulfuron - methyl was 0.0 5 ppm . The maximum storage duration for pot ato tuber samples was 279 day s (9.2 months). To support sample storage conditions and durations, storage stability study data were generated concurrently with the field trial study . These data demonstrate that residues of halosulfuron - methyl are stable i n/on fortified potato tuber stored frozen for up to 284 days (9.3 months). Residues of halosulfuron - methyl were below the LLMV (<0.05 ppm) in/on all samples of potato tuber harvested 42 to 46 day s following the second of two broadcast applications (soil f ollowed by foliar) of the 75% WG formulation of halosulfuron - methyl, made during fruiting with a total seasonal rate of 0.094 - 0.103 lb ai/A. Varying degrees of phy totoxicity (i.e., stunting, some chlorosis, slight browning of leaf edge) following applicat ion of halosulfuron - methyl were reported at some of the test sites (CA, CO, ND, and WI ). No phy totoxic effects were noted at the remaining trials. Although phy totoxicity appears to be attributed to the test substance application, these instances of phy to toxicity did not have an adverse impact on the residue trials.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 25 of 34 Conclusions : The submitted field trial data for halosulfuron - methyl on potato, the representative commodity

of Crop Subgroup 1C , reflect the use of a nonionic surfactant as recommended on the proposed label and approximate the proposed PHI . The data are also supported by concurrent storage stability

data. However, the number and location of field trials do not fully conform to the OPPTS 860.1500 guideline as only 14 trials were conducted whe reas the guideline requires a minimum of 16 trials to support a tolerance on Crop Group 1C. In addition, the potato data were generated using slightly

exaggerated rates of ~2.0 - 2. 1 X . ARIA will not require additional data on potatoes since additional tria ls at a 1 X rate will likely result in residues below 0 .05 ppm. The available data will support the proposed use pattern and ARIA recommends for a tolerance of 0.05 ppm for Crop Subgroup 1C. 860.1520 Processed Food and Feed Apple DER References: 477 721 06 .de r .doc An additional plot was established at the NJ site using a total seasonal rate of 0.484 lb ai/A ( ~5. 1X the proposed maximum seasonal rate), to generate samples for processing; however, as residues were nondetectable in any apple fruit sample, a processing study was not initiated. Conclusions . T hese data are adequate to conclude that additional apple processing study and tolerances for apple processed commodities are not required for this action. Potato DER Reference : 47772102.de2 Ina sin gle crop field trial conducted in WA during the 2004 growing season, two broadcast applications of a 75% WG formulation of halosulfuron - methyl, were made to bare soil and then to potato plants at the vegetative/fruiting growth stage, at 0.049 - 0.050 lb ai/A/application, with a 95 - day RTI , for a total rate of 0.099 lb ai/A ( 2 X the proposed maximum seasonal rate ) . Applications were made using ground equipment in a spray volume of ~18 gal/A, with an NI S included in the second application as an adjuvant. Matur e potato tuber was harvested at a 42 - day PHI and processed into granules/flakes, chips, and wet peel using procedures simulating commercial practices. Samples of potato tuber, granules/flakes, chips, and wet peel were analy zed for residues of halosulfuron - methyl as its RRE using the available tolerance enforcement method , Method RES 109 - 97 - 4, with modifications. The GC/NPD is adequate for data collection based on acceptable method validation and concurrent method recoveries. The LLMV for halosulfuron - methyl was 0.0 5 ppm in all potato matrices . The maximum storage durations of samples from harvest/processing to analy sis were 246 day s (8.1 months) for potato tuber and 251 - 300 day s (8.2 - 9.9 months) for potato granules/flakes, chips, and wet peel. To suppor t sample storage conditions and durations, a concurrent storage stability study was conducted with the processing study . These data demonstrate that residues of halosulfuron - methyl are stable for up to 284 day s (9.3 months), 3 02 day s (9.9 months), 297 day sHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 26 of 34 (9.8 months), and 288 day s (9.5 months) in/on frozen potato tuber, flakes/granules, chips, and wet peel, respectively . However, zero - day data were not provided . The results of the potato processing study are summarized in Table 7 . Residues of halosulf uron methyl were nonquantifiable (<0.05 ppm) in/on potato tuber harvested 42 days following the second of two broadcast applications of the 75% WG formulation of halosulfuron - methyl, made to soil and at the vegetative/fruiting growth stage at a total rate of 0.099 lb ai/A. Residues were also nonquantifiable in processed potato granules/flakes, chips, and wet peel, therefore, processing factors could not be calculated. Theoretical concentration factors based on loss of water (860.1520, Table 2) are 4. 7X fo r potato granules/flakes and, based on separation into components, 4. 0X for potato processed waste (860.1520, Table 3). The maximum theoretical concentration factor for potato is 5X (860.1520, Table 1). T able 7 . R esidue Data fromPotato Processing Stud y with Halosulfuron - me thyl . RAC Processed Commodity Total Rate (lb ai/A) PHI

(days) Residues (ppm) 1 Processing Factor Potato Tuber (RAC) 0.099 42 ND, ND -- Flakes/granules ND, ND Not calculated 2 Chips ND, ND Wet peel ND, ND 1 ND = Not d etected. Residues reported below the LOD (<0.0089 ppm in/on tuber; <0.0129 ppm in flakes/granules; <0.0307 ppm in chips; and <0.0402 ppm in wet peel). 2 Not calculated because r esidues were reported blow the LLMV (<0.05 ppm) in both the RAC and the proce ssed commodity. Conclusions . The submitted processing data for potato are acceptable. Residues of halosulfuron - methyl were nonquantifiable (<0.05 ppm) in/on potato tuber s following treatments at 2 X the proposed seasonal rate. Residues were also nonquantifiable in processed potato granules/flakes, chips, and wet peel . The Agency would have preferred that a trial with an exaggerated rate equal to or higher than the maximum theoretical concentration factor of 5X for potato have been conducted. However, b ecause of phy totoxicity limitations as reported in the magnitude of the residue trials, a new potato processing study will not be required. Based on these data, tolerances for potato processed commodities are not needed. 860.1650 Su bmittal of Analytical Reference Standards DP#250584, G. Herndon , 10/28/ 19 98 An an aly tical standard is currently available in the EPA National Pesticide Standards Repository for halosulfuron - methyl (expiration 6/14/ 20 13); however, a standard is not avail able for its 3 - CSA (3 - chlorosulfonamide acid) metabolite (personal communication with Dallas Wright, ACB, 2/23/ 20 09 ). ARIA notes that a standard for the RRE of halosulfuron - methyl is also required in support of the tolerance enforcement method for plant c ommodities. Analy tical reference standards of the 3 - CSA metabolite and the RRE must be supplied and supplies replenished as requested by

the Repository . The reference standard s should be sent to the Analy tical Chemistry Lab, which is located at Fort Mead e, to the attention of Theresa Cole at the following address: USEPAHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 27 of 34 National Pesticide Standards Repository /Analy tical Chemistry

Branch/OPP 701 Mapes Road Fort George G. Meade, MD 20755 - 5350 (Note that the mail will be returned if the extended zip c ode is not used.) 860.1850 and 860.1900 Confined /Field Accumulation in Rotational Crops DP# 225273 , G.J. Herndon , 10 /29 / 19 9 8 Metabolism Committee decision, G . Herndon , 5/21/ 19 96 DP#192510, G. Kramer , 8/30/1993 DP# s 188144 and 188814 , G. Herndon , 3/11/ 19 9 3 Acceptable confined rotational and limited field rotational crop studies were previously submitted. The results of both studies indicate that metabolites containing the py razole moiety may accumulate in harvested crops planted at intervals greater tha n one year. The confined rotational crop study , conducted at 0.19 lb ai/A, indicated that no measurable residues of halosulfuron - methyl were detected in any rotational crop commodities of wheat, soy bean, radish and lettuce at any

plantback interval (30, 1 20, and 360 day s after treatment). The limited field rotational crop study , conducted at 0.22 lb ai/A in a split (preplant + postemergence) application, with rotated crops of winter wheat, spring wheat, soy bean, sugar beet, and leaf lettuce indicated that no measurable residues of halosulfuron - methyl were detected in any field rotational crop samples, except in one spring wheat forage sample at 0.090 ppm (364 - day plantback interval). HED previously

concluded that the residue of concern in rotational crops is halosulfuron - methyl. Based on the absence of the parent compound in the confined studies and in the limited field rotational crop studies, with the exception of one forage sample, HED previously concluded that rotational crop tolerances and restrictio ns are not required for halosulfuron - methyl. Conclusion. The proposed use s on okra, pea and bean (succulent shelled and dried), tuberous and corm vegetables, and rhubarb are not expected to alter HED’s earlier assessment regarding the potential for inadv ertent residues in rotat able crops addressed in this registration action . No additional data are required. 860.1550 Proposed Tolerances Halosulfuron - methyl tolerance s for plant commodities have been established in 40 CFR § 180. 479 ( a ) (2) and are express ed in terms of halosulfuron - methyl, methyl 3 - chloro - 5 - [[[[(4,6 - dimethoxy- 2 - py

rimidinyl)amino] carbonyl] amino] sulfonyl] - 1 - methyl - 1 H - py razole - 4 - carboxylate . The proposed tolerance expression is consistent with the halosulfuron - methyl tolerances establis hed in 40 CFR §180.479(a)(2) and reflect the residues of concern as previously determined by

HED. Halosulfuron - methyl t olerances for livestock commodities are listed in 40 CFR §180.479(a)(1) and are expressed in terms of halosulfuron - methyl and its metabolites determined as 3 - chloro - 1 - methyl - 5 - sulfamoylpy

razole - 4 - carboxylic acid (also referred to as 3 - CSA, expressed as parent equivalents) .Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 28 of 34 Residues of halosulfuron - methyl were below the LLM V (<0.05 ppm) when the test formulation was applied to the proposed crops according to the conditions and parameters used in the field trials. The Agency ’s tolerance spreadsheet was not used for tolerance assessments and recommendations. For apples, the submitted data will support a RAC tolerance of 0.05 ppm . For blueberries, the submitted data will support a tolerance of 0.05 ppm for Crop Subgroup 13 - 07B (b ushberry

) provided the label for Sandea® Herbicide is amended to remove the instructions pertaining to the use of a non - ionic surfactant . If it is IR - 4’s intention to add a nonionic surfactant when Sandea® Herbicide is applied on Subgroup 13 - 07B, then additional field trial data are required. For okra, the available field trial data for fruiting vegetables will be translated to okra. The C hemSAC meeting of 10/18/ 20 06 has recommended the inclusion of okra in Crop Group 8 ( fruiting vegetables ). The ChemSAC has also determined that a separate tolerance for okra should be listed in the appropriate section of the CFR entry until the new crop gr oup regulation is published. The translated data support a tolerance of 0.05 ppm in/on okra. For Crop Subgroup 6B (p ea and b ean , s ucculent s helled ) , ARIA recommends a tolerance of 0.05 ppm , provided the proposed label s on Crop Subgroup 6B is amended to p rohibit applications to legumes grown for livestock feeds. Concomitant with the establishment of a tolerance for Subgroup 6 B, the individual tolerance for ‘bean, snap, succulent’ should be revoked. B ecause data are required for dried pea including the fo rages and hay of field pea cultivars for Crop Subgroup 6C ( dried s helled b ean ( e xcept s oy bean ) and p ea ), ARIA is unable to recommend for a registration and tolerance. When adequate residue data for dried peas become available, the petitioner may

again req uest a tolerance for Subgroup 6C . For rhubarb, the submitted data will support a RAC tolerance of 0.05 ppm . For potatoes, the submitted data will support a tolerance for Crop Subgroup 1C ( tuberous and corm vegetables ) at 0.05 ppm. The apple and potato p rocessing data indicate that tolerances are not needed for the processed commodities of these crops. Tolerances for halosulfuron residues of concern need not be established for the milk, meat, and fat of cattle, goat, hog, horse, and sheep as a result o f the proposed uses. The established tolerance of 0.1 ppm for the meat by products of cattle, goat, hog, horse, and sheep remain adequate. There are no poultry and swine feedstuffs associated with the recommended tolerances and crop uses . The petitioner should note that if additional uses are proposed in the future which would result in an increase in the dietary burdens, ARIA/HED will re - assess the adequacy of established animal tolerances. Table 8 presents the proposed/recommended tolerance level and the corrected commodity definition.Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 29 of 34 There are no Codex, Canadian, or Mexican maximum residue limits (MRL s) established for residues of halosulfuron - methy in crop or livestock commodities. An International Residue Li mit (IRL ) form is appended to this Summary Document and follows this section. Table 8 . Tolerance Sum ma ry for Halosulfuron - Methyl. Commodity (as Defined in Section F) Proposed Tolerance (ppm) Recommended

Tolerance (ppm) Comments ; C orrect Commodity D efinition PEA AND BEAN, SUCCULENT SHELLED, SUBGROUP 6B 0.05 0.05 ARIA recommends a label revision to prohibit applications to legumes grown for livestock feeds because no residue data are available for cow

pea forage and hay. Pea and bean, succulent shelled, subgroup 6B VEGETABLE TUBEROUS AND CORM , SUBGROUP 1C 0.05 0.05 Vegetable, tuberous and corm, subgroup 1C RHUBARB 0.05 0.05 Rhubarb P EA AND BEAN, DRIED SHELLED, EXCEPT SOYBEAN, SUBGROUP 6C 0.05 None Revised Section F. When adequate residue data for dried peas become available, the petitioner may again request a tolerance for Subgroup 6C. Pea and bean, dried shelled, except soybean, subgroup 6C APPLE 0.05 0.05 The proposed label should be amended to remove the instructions pertaining to the use of a non - ionic surfactant. Apple OKRA 0.05 0.05 The recommended t olerance is based on translation of data from fruiting vegetables . Okra B USHBERRY SUBGROUP 13 - 07B 0.05 0.05 The proposed label should be amended to remove the instructions pertaining to the use of a non - ionic surfactant. Bushberry subgrou

p 13 - 07BHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 30 of 34 References DP#s: 173627 & 180565 Subject: PP#2G4073. Temporary Tolerance Petition and Experimental Use Permit for Use of MON 12000 (Permit ® ) on Corn; 000524 - EUP - TO. Evaluation of Analy tical Method and Residue Data. From: G. Herndon To: J. Miller/D. Kenny and A. Kocialski Dated: 7/30/ 19 92 MRIDs: 42139400 - 08 DP#: 181023 Subject: 000524 - EUP - TA. Experimental Use Permit for Use of MON 12000 and MON

13900 Together as MON 12041 (Battalion®) on Corn; Evaluation of Analy tical Method and Resid

ue Data. CBTS#: 10295. From: G. Herndon To: J. Miller/D. Kenny and A. Kocialski Dated: 11/12/ 19 92 MRIDs: 42396202 and 42396203 DP#s: 184435 Subject: PP#2G4073. Temporary Tolerance Petition and Experimental Use Permit for Use of MON 12000 (Permit ® ) on Corn; 000524 - EUP - TO. Amendment of 7/30/92 Addressing Analy

tical Method and Residue Data Deficiencies. CBTS#: 10948. From: G. Herndon To: J. Miller/D. Kenny and A. Kocialski Dated: 1/15/ 19 93 MRIDs: 42538400 - 42538404 DP#s: 188144 & 188814 Subject: PP#2G4073 . Temporary Tolerance Petition and Experimental Use Permit for Use of MON 12000 (Permit®) on Corn; 000524 - EUP - TO . Amendment of 2/10/93 Addressing Analy

tical Method and Proposed L abel Deficiencies . Impact of the Co nfined Rotational Crop Study Results (EFGWB) on this EUP Request . CBTS#: 11374 and 11451. From: G. Herndon To: J. Miller

/D. Kenny and A. Kocialski Dated: 3/11/ 19 93 MRIDs: NoneHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 31 of 34 DP#: 192510 Subject: ID # 000524 - UAT. Review of limited field rotational study of MON 12000 [3 - chloro - 5 - [[[[(4,6 - dimethoxy- 2 - py rimidinyl)amino]carbonyl]amino] - sulfonyl] - 1 - methyl - 1H - py

razole - 4 - carboxylic acid, methyl ester]. Case 023936. CBTS# 12079. From: G. Kramer To: J. Miller Dated: 8/30/ 19 93 MRIDs: 42812104 DP#s: 189198, 198051, 189189, 189178, 189183 & 189195 Subject: PP#3F04193. Permanent Tolerance Request for Use of MON 12000

(Halosulfuron) on Field C orn and Grain Sorghum (Milo). Evaluation of Analy tical Method and Residue Data. From: G. Herndon To: J. Miller/D. Kenny and A. Kocialski Dated: 3/8/ 19 94 MRIDs: 42661401 - 07, 43042601 - 02 DP#: 204062 Subject: PP#3F04193. Sectio n 3 Registration and Permanent Tolerance Request for Use

of MON 12000 (Halosulfuron) on Field Corn and Grain Sorghum (Milo). Submission Received 2/24/93 Addressing Deficiencies in the Nature of the Residue in Plants and Animals. CBTS# 13817, 13861. From: G. Herndon To: J. Miller/D. Kenny and A. Kocialski Dated: 6/22/ 19 94 MRIDs: 42678001 - 03 DP#: 198361 Subject: PP#4G04279 and 524 - EUP - 74 - EUP and Temporary Tolerance Request for the New Chemical MON 12000 on Sugarcane and Sorghum . CBTS No. 13092. From: G. Otakie To: J. Miller/D. Kenny and A. Kocialski Dated: 7/21/ 19 94 MRIDs: 42991201 - 02Halosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 32 of 34 DP#: 202131 Subject: PP#3F04193. Section 3 Registration and Permanent Tolerance Request for Use of

MON 12000 (Halo sulfuron) on Field Corn and Grain Sorghum (Milo). Submission Received 3/29/94 Addressing Deficiencies in the Regulatory Enforcement Method for Animal Products and the Proposed Section F. CBTS# 13568 From: G. Herndon To: J. Miller/D. Kenny and A. Koci alski Dated: 10/4/ 19 94 MRIDs: 43195001 and 43177501 DP#: 214890 Subject: PP#3F04193. Halosulfuron (MON 12000) on Animal Commodities. Results of

the Petition Method Validation Request. CBTS# 15480. From: G. Herndon To: J. Miller/D. Kenny and J. Smith Dated: 5/3/ 19 95 MRIDs: 43195001 DP#: None Subject: Halosulfuron (MON 12000). The HED Metabolism Committee Meeting Held on

May 20, 1996. From: G. Herndon To: HED Metabolism Committee Dated: 5/21/ 19 96 MRIDs: None DP#: 250584 Subject: PP#6F4620 and 8F4937. Halosulfuron - methyl on Various Commodities. Results

of the Petition Method Validation Request for the Proposed Enforcement Method. From: G. Herndon To: V. Walters/ J. Tompkins Dated: 10/28/ 19 98 MRIDs: 44495801 and 44555901 DP#: 225273 Subject: Halosulfuron. Revised Section F Proposing Deletion of Existing Rotational Crop

Tolerances. From: G. Herndon To: V. Walters/ J. Tomp kins Dated: 10/29/ 19 98 MRIDs: NoneHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 33 of 34 DP#: 223801 Subject: PP6F4661. Section 3 Registration and Request for Permanent Tolerances for

Halosulfuron - methyl on Sweet Corn and Popcorn. Evaluation of Analy tical Methods and Residue Data. From: M. Doherty To: J. Tompkins/V. Walters Dated: 11/17/ 19 98 MRIDs: 43918501 DP#: 251007 Subject: PP8F4937. Request for Permanent Tolerances for Halosulfuron - methyl on

Cotton, Rice, Pistachio Nuts, and Tree Nut Crop Group (Crop Group 14 as listed in 40 CFR 180.41). Eva luation of Metabolism of Halosulfuron - methyl in Soy bean. From: M. Doherty To: J. Tompkins/V. Walters Dated: 12/10/ 19 98 MRIDs: 44689501 DP#: 267423 Subject: PP# 0F06169. Halosulfuron - methyl on Fruiting Vegetables (Except Cucurb its)

Crop Group 8/ Review of Analy tical Methods and Magnitude of Residue Data. From: A. Acierto To: J. Tompkins/V. Walters Dated: 4/25/ 20 02 MRIDs: 45117501, 45117502 DP#: 278587 Subject: PP# 1E06322. Hal osulfuron - methyl on Bean, Dry and Bean, Snap. Magnitude of Residue Data. From: A. Acierto To: R. Forrest/S. Brothers Dated: 6/15/ 20 02 MRIDs: 45 427801, 45427802 Attachments: International Residue L imit St atus sheetHalosulfuron - methyl Summary of Analytical Chemistry and Residue Data DP#367058

Page 34 of 34 

## INTERNATIONAL RESIDUE LIMIT STATUS Chemical Name: methyl 5 - [(4,6 - dimethoxy - 2 - pyrimidinyl)amino]carbon ylaminosulfonyl - 3 - chloro 1 - methyl - 1 H

- pyrazole - 4 - carboxylate Common Name: Halosulfuron - methyl X Proposed tolerance □ Reevaluated toler ance □ Other Date: 10/2009

Codex Status (Maximum Residue Limits) U. S. Tolerances X No Codex proposal step 6 or above □ No Codex proposal step 6 or above for the crops requested Petition Number: PP# 9E7577 DP#: 367058 Other Identifier: Residue de finition (step 8/CXL): N/A Reviewer/Branch: P. Deschamp, N. Dodd/RAB3 Residue definition: halosulfuron - methyl Crop (s) MRL (mg/kg) Crop(s) Tolerance (ppm) Pea and bean, succulent shelled, Subgroup 6B 0.05 Vegetable, tuberous and corm, Subgroup 1C 0.05 Rhubarb 0.05 Pea and bean, dried shelled, except soybean, Subgroup 6C 0.05 Apple 0.05 Okra 0.05 Bushberry, Subgroup 13 - 07B 0.05 Limits for Canada Limits for Mexico X No Limits □ No Limits for the crops requested X No Limits □ No Limits for the crops requested Residue definition: N/A Residue definition: N/A Mexico defers to Codex MRLs or US tolerances for its export purposes. Crop(s) MRL (mg/kg) Crop(s) MRL (mg/kg)

Notes/Special Instructions: S. Funk, 10/15/2009.